Functionalized isothianaphthene monomers that promote quinoidal character in donor-acceptor copolymers for organic photovoltaics

Jessica D. Douglas, Gianmarco Griffini, Thomas W. Holcombe, Eric P. Young, Olivia P. Lee, Mark S. Chen, Jean Frechet

Research output: Contribution to journalArticlepeer-review

37 Scopus citations

Abstract

A series of low band gap isothianaphthene-based (ITN) polymers with various electron-withdrawing substituents and intrinsic quinoidal character were synthesized, characterized, and tested in organic photovoltaic (OPV) devices. The three investigated ITN cores contained either ester, imide, or nitrile functionalities and were each synthesized in only four linear steps. The relative electron-withdrawing strength of the three substituents on the ITN moiety was evaluated and correlated to the optical and electronic properties of ITN-based copolymers. The ester- and imide-containing p-type polymers reached device efficiencies as high as 3% in bulk heterojunction blends with phenyl C 61-butyric acid methyl ester (PC 61BM), while the significantly electron-deficient nitrile-functionalized polymer behaved as an n-type material with an efficiency of 0.3% in bilayer devices with poly(3-(4-n-octyl)phenylthiophene) (POPT). © 2012 American Chemical Society.
Original languageEnglish (US)
Pages (from-to)4069-4074
Number of pages6
JournalMacromolecules
Volume45
Issue number10
DOIs
StatePublished - May 3 2012

ASJC Scopus subject areas

  • Materials Chemistry
  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry

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